I can't speak to the kiteability of the area (I just started kiting this year), but be certain to stop at The Fish Market in Koloa and grab some poki or a plate lunch. Both of which are some of the best on the island!

I've kited Kawailoa Bay. It's just east of the Haytt in Poipu. Drive down the dirt roads into the park/preserve area and park when the road meets the bay. Walk out to the sandy point to launch and there is fun wave kiting off the point. Beware it is a shallow reef and can get heavy, so I would say this is a fairly advanced spot.

You'll probably have a car anyway, so don't rule out a little bit of driving. Normal trade winds will be coming from the other side of the island and may not make it the Poipu area. But Poipu and surrounding area (and Waimea canyons, etc.) are cool so check that out too. But if you get in the car and drive a bit you can start with "Baby Beach" near Lipoa, then Anini Beach, which is an awesome reef protected more or less flat water spot on a higher tide. Go through the reef to visit the outside blue water. Farther down on North shore, you can go just past Hanalei Bay and self launch at te beach area near Hanlei Bay Colony, and then just a tiny bit farther is Tunnels/y-Camp, be sure to ask locals for info first, be aware, humble., etc.

I kited Mahalepu for five straight days in January. As stated before, drive down the dirt road past the Hyatt and either park at Gillan House or continue down to the larger parking area about 1/2 mi further. In between the two is a point that is protected by a reef. Watch for beach goers and launch in this area then work outside to the west side of the reef for some waves. There were two locals kiting there who were very helpful.

Thanks for all of the advice. Looks like I am going to have to watch the tides given alot of these spots have shallow reef. Also hadn't thought about kiting Mahalepu, but might as well if I can sneak away from family activities for 2 hrs.

For those of you that mentioned down-winders from Hanalei to Tunnels - did you arrange a shuttle back, or just drive a car down there?